(1S,2R,4R,7S,8R)-7,8-Bis-benzyloxymethyl-4-methyl-2-vinyl-bicyclo[2.2.2]oct-5-en-2-ol

Base Information

Chemical Name:(1S,2R,4R,7S,8R)-7,8-Bis-benzyloxymethyl-4-methyl-2-vinyl-bicyclo[2.2.2]oct-5-en-2-ol
CAS No.:176659-55-5
Molecular Formula:C₂₇H₃₂O₃
Molecular Weight:404.549
Hs Code.:

Synonyms:(1S,2R,4R,7S,8R)-7,8-Bis-benzyloxymethyl-4-methyl-2-vinyl-bicyclo[2.2.2]oct-5-en-2-ol

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Chemical Property of (1S,2R,4R,7S,8R)-7,8-Bis-benzyloxymethyl-4-methyl-2-vinyl-bicyclo[2.2.2]oct-5-en-2-ol

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Technology Process of (1S,2R,4R,7S,8R)-7,8-Bis-benzyloxymethyl-4-methyl-2-vinyl-bicyclo[2.2.2]oct-5-en-2-ol

There total 8 articles about (1S,2R,4R,7S,8R)-7,8-Bis-benzyloxymethyl-4-methyl-2-vinyl-bicyclo[2.2.2]oct-5-en-2-ol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 61.0%

: 1826-67-1
vinyl magnesium bromide

: 176659-54-4
(1S,4R,7S,8R)-7,8-Bis-benzyloxymethyl-4-methyl-bicyclo[2.2.2]oct-5-en-2-one

: (1S,2S,4R,7S,8R)-7,8-Bis-benzyloxymethyl-4-methyl-2-vinyl-bicyclo[2.2.2]oct-5-en-2-ol

: 176659-55-5
(1S,2R,4R,7S,8R)-7,8-Bis-benzyloxymethyl-4-methyl-2-vinyl-bicyclo[2.2.2]oct-5-en-2-ol

Guidance literature:: In tetrahydrofuran; at 0 ℃; for 3h;
DOI:10.1039/cc9960000869

Reference yield:

: 114763-30-3
(3aR,7aS)-2,2,4-trimethyl-3a,7a-dihydro-1,3-benzodioxole

: 176659-55-5
(1S,2R,4R,7S,8R)-7,8-Bis-benzyloxymethyl-4-methyl-2-vinyl-bicyclo[2.2.2]oct-5-en-2-ol

Guidance literature:: Multi-step reaction with 8 steps

1: 68 percent / CH₂Cl₂ / 24 h / 0 - 18 °C

2: 88 percent / LiAlH₄ / tetrahydrofuran / 3 h / 66 °C

3: 99 percent / NaH, Bu₄NI / dimethylformamide / 18 h / 0 - 18 °C

4: 100 percent / aq. AcOH / 16 h / 80 °C

5: 97 percent / 4-AcNH-TEMPO, p-TsOH / CH₂Cl₂ / 3 h / 18 °C

6: 92 percent / pyridine / CH₂Cl₂ / 18 h / 18 °C

7: 88 percent / SmI₂, AcOH / tetrahydrofuran / 0.33 h / 18 °C

8: 61 percent / tetrahydrofuran / 3 h / 0 °C

With pyridine; 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl; lithium aluminium tetrahydride; samarium diiodide; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; acetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1039/cc9960000869

Reference yield:

: 176659-49-7
((1S,2S,6R,7R,8R,9S)-9-Hydroxymethyl-4,4,7-trimethyl-3,5-dioxa-tricyclo[5.2.2.0^2,6]undec-10-en-8-yl)-methanol

: 176659-55-5
(1S,2R,4R,7S,8R)-7,8-Bis-benzyloxymethyl-4-methyl-2-vinyl-bicyclo[2.2.2]oct-5-en-2-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 99 percent / NaH, Bu₄NI / dimethylformamide / 18 h / 0 - 18 °C

2: 100 percent / aq. AcOH / 16 h / 80 °C

3: 97 percent / 4-AcNH-TEMPO, p-TsOH / CH₂Cl₂ / 3 h / 18 °C

4: 92 percent / pyridine / CH₂Cl₂ / 18 h / 18 °C

5: 88 percent / SmI₂, AcOH / tetrahydrofuran / 0.33 h / 18 °C

6: 61 percent / tetrahydrofuran / 3 h / 0 °C

With pyridine; 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl; samarium diiodide; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; acetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1039/cc9960000869